| Identification | Back Directory | [Name]
jolkinolide B | [CAS]
37905-08-1 | [Synonyms]
jolkinolide B
1,4-dibutyl-N-(2,6-dimethylphenyl)piperazine-2-carboxamide,nitrous acid
(4aR,6aS,7aβ,10aR)-1,2,3,4,4aα,5,6,11aβ,11bα,11c-Decahydro-4,4,8,11cβ-tetramethylbisoxireno[1,10a:3,4]phenanthro[3,2-b]furan-9(7aH)-one
Bisoxireno[1,10a:3,4]phenanthro[3,2-b]furan-9(7aH)-one, 1,2,3,4,4a,5,6,11a,11b,11c-decahydro-4,4,8,11c-tetramethyl-, (4aR,6aS,7aR,10aR,11aR,11bR,11cR)- | [Molecular Formula]
C20H26O4 | [MDL Number]
MFCD28387432 | [MOL File]
37905-08-1.mol | [Molecular Weight]
330.42 |
| Chemical Properties | Back Directory | [Melting point ]
213-215℃ | [Boiling point ]
497.1±45.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
-10 to -25°C | [solubility ]
DMSO: 2mg/mL, clear (Warmed) | [form ]
Solid | [color ]
White to off-white | [InChI]
InChI=1S/C20H26O4/c1-10-12-14-19(22-14)9-6-11-17(2,3)7-5-8-18(11,4)13(19)15-20(12,23-15)24-16(10)21/h11,13-15H,5-9H2,1-4H3/t11-,13+,14-,15-,18-,19+,20-/m1/s1 | [InChIKey]
SOVOCMGDFRGRKF-MCDHERAVSA-N | [SMILES]
O1[C@@]32OC(=O)C(=C3[C@H]4O[C@]54[C@@H]([C@H]21)[C@]6([C@@H](C(CCC6)(C)C)CC5)C)C |
| Hazard Information | Back Directory | [Uses]
Jolkinolide B, a bioactive diterpene isolated from the roots of Euphorbia fischeriana Steud, is known to induce apoptosis in cancer cells[1]. | [Definition]
ChEBI: A natural product found in Euphorbia fischeriana. | [Biological Activity]
Jolkinolide B is a diterpenoid isolated from the dried root of Euphorbia fischeriana steud th at exhibits anticanceranti-inflammatory and immunomodulatory activities. Jolkinolide B induces apoptosis in numerous human cancer cell lines including breast cancer MDA-MB-231MCF7chronic myeloid leukemia K562leukemic U937 and LNCaP cells. Apparentlyit induces apoptosis in mouse melanoma B16F10 cells through downregulation of mRNA expression. | [References]
[1] Wang, J., Zhou, Y., Bai, X. et al. Jolkinolide B from Euphorbia fischeriana Steud induces apoptosis in human leukemic U937 cells through PI3K/Akt and XIAP pathways. Mol Cells 32, 451–457 (2011). DOI:10.1007/s10059-011-0137-0 |
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